For those of you who like a points system...
+150pts keeping the neighborhood free from any new last names
+20pts for every marriage uniting two sims with the last names above.
-20pts for every townie married.
-25pts unnatural death [it's too tempting!]
+5pts natural death
+5pts for each family friend at the time of death. [must have the family symbol + the friend symbol]
+10pts for each drama plot twist (note: this neighborhood is known for drama, affairs, mysterious deaths and disappearances. keep it going! da da duh!)
+20pts for having a family feud or two families feuding against each other over something small or big.
+250pts having the blood lines so intertwined that at the end that each sim heir can say they have each of the last names heritage.
+50pts if you have sims matched up differently then you ever have played them before.
+10pts every time you extend a sims life so they can see their great grandchildren's kids.

Side Game Points
+25pts include a government with taxes, fees, and laws. [realistic]
+15pts include a job shortage. [not everyone can be a rock god...]
+10pts realistic career skills to jobs [if you never went to University, I doubt you would become a Teacher at the High School]
+15pts no 20k handouts [that's right, either the parents help the kids out or it's apartment living until they make mo' money]
+50pts charge tuition, books / supplies, dorm etc fees for university. $$$ student loans available of course. mwaha
+10pts once a year have a family holiday [Thanksgiving / Christmas / New Year's / Easter] or a vacation
+50pts have at least one birthday party for each offspring. So either when they turn toddler, child, teen, adult or senior. Just once.
+50pts have at least one life party for each offspring. Get into private school, graduation, uni grad, get engaged, stag / hen, wedding, baby shower, anniversary
+50pts map out a life for the sim. Friends? Hobbies? Interests? Values? Passion? Who they are, what they stand for, what they aspire to.. & stick to IT!
+150pts make clubs / cliches / networks / guilds and decide what sims fit what grouping. Make community lots for each or designate one as the hangout.
do they wear a certain type of clothes? Do they work in the same career field? Do they have the same interests? What brings them together?
+40pts set business hours for each community lot and stick to them. [I don't know any store other than 7-eleven that is open 24/7]
+50pts ROS once a year +100pts once a season +250pts once a season and it is all negative [roll action brings no point deductions]
+75pts create hoods in the hood. Take Vancouver, BC for instance. We have Kitsilano {rich/beach} Commercial Drive {hip/up&coming} Hastings {poor}
do the creatives live there? The career driven? The families? The younger crowd? Price the lots / houses accordingly. Make a skid row up to Mansions.

I like this! My attention span is almost always too short for me to ever finish a 10 generation legacy (it doesn't help that tomorrow I'll start university, so of course the perfect timing to begin a new Sims game), but this is tempting enough for me to at least want to try

*squeals I am so excited that this challenge was approved and that to my surprise Marka93 has already started! So excited.

Marka93 : indeed! I'm almost tempted to start over... A hood with no townies though is awesome but in later generations I think everyone will become family through marriage that your going to need a townie or two. Very cool hood though playing the ancestory! I'm not familiar with some of the names. Danders? Marsh? Could you tell us about the family tree?

Carooh : you should join in for sure! I know my attention span is bad too. I like to create new things all the time. But just imagine all the dramatic story telling pleasantview would provide.

Here is how I matched people up...

Mary-Sue & Daniel
Daniel broke up with Kaylynn, rejuvenating their marriage, had twins [Morgan & Levi], He left his job as the coach to be a stay at home dad.

Angela & Dustin
I know, how original, but Angela did marry an old townie guy who died before finally getting with Dustin

Lilith & Dirk
Lilith ran away & lived in a cabin, meeting up with Dirk, got pregnant, drop out. Dirk left her but then came back & married her

Dina & Mortimer
Dina owns the fine dining restaurant. Mortimer is young again. He created the [Elixir of Life] in search for staying alive for Bella.

Darren & Kaylynn
Darren took the last name Langarek.

Brandi & Benjamin
Brandi had an affair with John Burb. She was lonely and he was too since he was going through empty nest with Lucy gone since he was a stay at home dad. They both met at church. Jennifer, John's wife is the Pastor. It wasn't until Brandi became pregnant that they realized they couldn't do this anymore and received help from the deacons of the church for counselling. It was agreed that since Brandi didn't have the money or the ability to stay at home with the baby, that John & Jennifer would raise the baby and Jennifer adopt. Jennifer found it hard but she forgave him, embraced the baby and they are happy.
Brandi lost respect with Dustin when he found out but Beau and Riley seemed more understanding. After awhile she met a townie named Benjamin and got married.

John & Jennifer

Herb & Coral

Bella Goth
phoned her up and moved her back to pleasantview. Strangely, she is still young.

Beau Broke & Alexander Goth
they met in high school, went to college together and then moved out together

and last... well this is a bit hard to explain and heck you may not want to read. [adult] I'm a bit wacky sometimes going far fetched.

The big love triangle, Nina & Don | Don & Cassandra.
I believe that Nina understands Don because she is a romance sim herself. However, she did break it off with him but they had trysts resulting in unplanned parenthood. 3 to be exact. He married Cassandra and moved into the Goth Mansion. He tried to be true, but couldn't. He felt the weight of Mortimer's glare and the expectations of Cassandra for a family and love. He felt boxed in and rebelled. He used Mortimer's money and bought a nightclub. He told Cassandra he was working hard to provide a future for their family which they did have 2 kids, but he mostly used it as a way to pick up chicks. She hardly saw him, she was a stay at home mom for the early years. He was busy. She was so obsessed with loving him that it was stifling him. Don does love Cassandra but not in a deeply romantic way. However, Nina was always the one he would go to. So he left Cassandra, divorced her, they had their day in court, child support figured out, 50 / 50 divided and he moved in with Nina. Now Nina had taken on escorting shall we say to pay the bills and support her 3 kids. So Don and her had an open arrangement which worked best for both romantic sims. However, after awhile Nina got older and decided to stop her nightly visits. Her kids were not so young anymore and they would put two and two together. So Don and her settled into family life still with romance on the side. Cassandra wouldn't let go of Don. Mortimer had forbid her to see him but she just knew that she had to be with Don.

[See, Don was the only one when she was a teenager, in high school who looked her way. She was a nerdy academic with thick glasses and pigtails. She dressed really old fashioned and weird. No one paid attention to her and then the day that Don noticed her it was like a ray of sunshine floated down from the heavens on her. Her whole life lit up. With Don around her, people started to notice her. She felt dazzled when he gave her even the smallest attention.]

So wanting to have Don in her life, and for her kids to have their father, she did a desperate act. She told him that she wanted to be with him no matter how it happens and in what way. Seeing Cassandra so torn and how his leaving her had devastated her life he decided to talk to Nina and she agreed, being the open romantic sim she is, Cassandra and her kids would move in with them. So yes, Nina, Don & Cassandra with their offspring live together. Nina & Don share a bedroom upstairs, and Cassandra & Don share a bedroom downstairs. They pooled their resources and live in a pretty nice house. For awhile, Cassandra hated it but would do it just to be with Don. She saw Nina as the enemy but would keep that to herself until one day she realized she liked it. Her kids had other kids to grow up with, they had a big house with everything they needed, she realized if it wasn't Nina it would have been someone else because Don is a lover. She liked that she had a big family and independence since someone was always able to watch the kids. In addition to her being happy, Don and Nina were too. With no restrictions they both felt they could have all they wanted. Later in life they really settled down into family life with 5 children in the house and work that not many outside lovers happen. [current situation]

Additional info : disclaimer maybe a weird twist.

Daniel was with Kaylynn because she understood him. He didn't want to have to act like the macho athlete guy, the stereotype of a sports coach when he felt more feminine. However, once he broke it off with Kaylynn he told Mary-Sue everything. She accepted his feelings and after that he wore longer hair and makeup. [If I could find men's women clothes he would wear them too] Herb, Mary-Sue's dad and the deacon of the church was already upset about his affair and then with Daniel's transformation he was quite against Daniel and wouldn't look his way. Daniel made a great stay at home dad. He was very emotional when the twins moved off to university.

As for townies I have attached Downtown to have some townies for the later years plus I will be able to bring back the Tricous' with the 6 teens that live there.http://sims.wikia.com/wiki/Tricou_family

4th pic is Tango Caliente held by Tariq Al Mahmoud.
5th pic is Nighat Al Mahmoud held by Dulcinea Caliente.
6th pic is Flamenco Caliente held by Nestor Caliente with his other daddy standing near by Pollination Technician 7.

After Flamenco becomes of toddler I will use an in-game skintone changer and set his skintone to what it was in Pleasantview.

I played this household in the wrong time frame so we will not see them again until Mortimer Goth has been born and made it to his teen years.

In the time line I have all of the 2nd gen born with a few of the 3rd gen already born and will have to wait on them to let the 2nd gen catch up. (For this challenge there all 2nd gen.)

Not only am I using Maxis made but deleted sims that I fixed and brought back to life I am also using all Maxis houses from both Sims 1 and Sims 2.
All houses have been rework by me and some of them come from the Riverside hood that I fixed and remade from scratch. http://modthesims.info/download.php?t=503756
(I have 4 of my own houses here to but they will be gone and the org. Pleasantview houses will take there place in this hood.)

Mortimer and Bella Goth will start there life together in there Sims 1 house that I made for Old Town http://modthesims.info/download.php?t=522506
Bod and Betty Newbie will also start out in there Sims 1 house.
Michael Bachelor after collage will start out in that single bedroom house for Sims 1, the one that was in front of Bob and Betty's house in Sims 1.

Here is a pic of the hood layout for now and it might change over time.

I will use this post for all 2nd generation child pictures. When they become teenagers I will do make overs to match how EA/Maxis has them. I have decided to leave them as they are until they grow up to adulthood.

Starting with Gunther and Firda Goth.
Adding in Agnes and Cornelia Crumplebottom.

At the start I had a bit of trouble figuring out what to do with the Oldies: While they already have grandchildren at the start of the game there is no heir to the family name. And with them being elders that's not very likely to change. I could have changed the last name of one of their offspring (e.g. if Mary Sue would find out about Daniel's affair she could divorce him and change her last name back to her maiden name) but that felt too cheaty. Of course there's always adoption but even if they'd adopt a child (as opposed to a toddler or baby) they'd probably both be dead before the child reaches adulthood.

And then it hit me and they ended up being the first family that I've played for this challenge So here's some pictures of the Oldie's week under the spoiler:

So this is their house. Guess what I'm trying to achieve here...

If after the last picture you were thinking "PlantSim" you were correct.
Fun fact: It was Herb who did most of the work in the garden (his OTH is nature) but Coral who was turned.

And in true Family-Sims-fashion Coral immediately rolled the want to spawn a plant baby.

Played the Pleasant's first week. Note that I use Tarlia's fixed neighborhoods which got rid off the pre-scripted events. So Mary-Sue didn't get fired/demoted and is still blissfully unaware of Daniel's affair with the maid.
Pictures under the spoiler - at least of Daniel and Mary-Sue; it seems like I've failed to take any photos of Angela or Lilith (not that anything interesting happened to them but still).

Daniel and Mary-Sue rekindle their relationship.

Daniel: "So...wanna woohoo?"
Actually this picture's lying. It was Mary-Sue who had the woohoo want not Daniel.

Mary-Sue: "Great idea! Let's do it!"

You can see by Mary-Sue's different outfit that a baby is on the way. Unfortunately we won't see it before their next rotation.
(I play monday-monday-rotations but the Pleasants start on a thursday so their "week" was only 4 days long. That's also why I sent them on vacation, I wanted more time with the family.)

Outtake from the Burb's week: Daniel, are you sure it's a good idea to invite both your wife and your mistress to an outing? That's just asking for trouble.
I let Jennifer end the outing as fast as I could but Kaylynn still caught Daniel "cheating" on her with his wife. Oh well...

Since this is the last post I will use this one to upload pics of the Tricou sims that will marry the extra Pleasantview sims.

To start it out with Don Kosmokos (aka Orion Teens) without the makeup he starts out with and he will marry Frida Goth. (I might change his last name to Tricou but I am not sure yet.) Update, I went ahead and changed his last name to Tricou and will also do it for the other male teens, the female Tricou teens will carry the last name of the extra Pleasantview sims.

Some info, After both Frida and Agnes did the scope room they both went and flirted with there lover all by themselves so they told me who they wanted.

Moving in. John immediately etablishes himself as a complete jerk by refusing to play with Lucy. Hrmpf!
Bad move, John. See if I attemp to fullfil your LTW now.
(to be honest I probably wouldn't have anyway 'cause he has the dreaded 'raise 20 puppies/kittens'-LTW. But now I don't even want to try anymore)

Lucy brings home Alexander Goth from school. They are the same age so that makes him the #1 candidate for her future spouse. Not exactly a rare pairing but there isn't much of a choice left if all playables are supposed to marry other playables.
Alexander likes to hang out in her parents' bedroom. Soon after this picture was taken they shooed him out to have some private time. He left - and wandered back in before the woohoo-animation was even over.

Another Burb is on the way.

Lucy grew up. She shares her aspiration with John - and sadly also her LTW. Whyyyyyyyyyyyy?

Lana Burb is born.
Everyone: "Yay! Baby!"
Lucy's totally faking it though - her relationship with her sister starts out negative.

I'm currently planning to start a new game in Pleasantview, so I might try this - just one question though, are worldbuilder types who wouldn't touch "realism" with a ten foot plumb bob welcome here? Because that's definitely the way I play, I love creating different cultures and customs for my hoods and hate trying to recreate modern earthly life. If that's perfectly fine, I will quite happily join in and ramble on about my personal headcanon till the cowplants come home.

Goth :
As usual Cassandra's wedding was a disaster. After that she decided to get a makeover and went on rebound, starting an impormtu relationship with Darren Dreamer (she even moved in with him and Dirk). Mortimer meanwhile caught Dinah in bed with Don and called off his own engagement to her. He then tried to romance Coral Oldie, but she wouldn't have any of it After that he pretty much gave up and committed himself to studying music instead, both on the piano and, strangely enough, the synthesizer. Alexander slowly came out of his shell after becoming a teen and is amassing a surprising amount of friends. The biggest problem will be that I can't send him to university after Mortimer passes on without losing the Goth Manor, so he won't go.

Pleasant :
As usual Mary-Sue caught Daniel in bed with Kaylynn and threw him out on the street. After that all three Pleasant women took to running the whole household by themselves. Mary Sure got a haircut and continued climbing up the career ladder. Lilith developed political ambitions of her own (she dreams of becoming Mayor) and Mary-Sue got her a part-time job as a door-to-door poller. Of course taking on such a public job Lilith had to tone down her Gothic attire considerably (she did however die her hair black). Angela meanwhile is doing well as home maker and gardener. On the last day of the rotation something unusual happened; Daniel waltzed into the house and sat down to dinner with his ex-wife and daughters. During this Daniel and Mary-Sue actually rekindled their romance...

Oldie:
This was something completely new to me... never actually played the Oldies much before taking on this challenge. However, presented with the dilemma to find a way to preserve the family name I had them adopt a kid; a boy named Gerard. For now they all get along very well with each other, I just hope he'll age up into a teen before both Herb and Coral croak. Would moving him and Coral to live with Mary-Sue cause me to fail the challenge?

Broke:
Brandie actually went into aspiration failure from changing the diapers of her third son (Buddy, I know, terrible name, but its meant to sound terrible and redneck). Aside from that nothing much iof interest happened, this is a family that will only get really interesting later on, like when Dustin marries Angela and the two of f them learn that, due to his criminal record, nobody will hire him...

Burb:
John and Jennifer both started working at a law firm... then of course Jenn got pregnant and eventually gave birth to their second daughter (Vanessa). John is also cultivating a Garden, like his bio suggests. John's life-time wish is to graduate 3 children from uni...I might even fulfill it.

Dreamer:
Cassandra moved in, married Darren and they had a son called Kent. With Darren now actually being a successful painter and Mortimer presenting Cassandra with a generous sum for a wedding gift, they were able to expand their house considerably. Cassandra is currently pregnant with their second child.

Langerak :
Daniel and Kaylynn moved into a seedy condo, Kaylynn got a job as security guard and later gave birth to twin girls (Rose and Melissa-May) this is Daniels second set of twin girls, after Lilith and Angela Of course Daniel rekindled his relationship with Mary-Sue behind Katelynn's back and even got engaged to his ex-wife. Finally he revealed this to Kaylynn and they broke up. I'm planning to move Kaylynn and her girls into an apartment in downtown next rotation.

Lothario and Caliente:
While drunk at a party, Don ended up making out with Nina, right in front of Dina's and Kaylynn's eyes, he also ended up knocking her up. Him being traditional like that he insisted that Nina would marry him so that their child would have his last name. It ended up a son named Ron. Meanwhile, Dina, realizing that nobody was going to just give her a life of luxury smartened up and started working in the Architecture career, as far as continuing her family name I have plans for her, she'll be one of the Sims I will put into unusual pairings I haven't tried before. But that's still a while off, I hope she'll have a desk job by then.